Miss Information

I recently decided to get in touch with a guy I had shared a night with a few years back. We went to university together and had mutual friends, so I sent him a chatty message asking how he was doing and apologizing for/joking about the night we spent together. (We were sloppy drunk and my recollection is hazy at best). I'd always had a bit of a "what if…" about this guy, and I suppose I was curious to see if he remembered me.

As it happened, he remembered that night pretty well — possibly better than I did — and we began IMing regularly for hours at a time. From a quick perusal of his Facebook I was vaguely aware that he had a girlfriend but he never brought her up. I let this lie for a while, thinking the chats were fairly harmless anyway.

Then, the other night, things started to get pretty flirty. After we'd been talking for two hours, I decided one of us should address the girlfriend-shaped elephant in the room. "Does your girlfriend mind you chatting with me?" I asked, and he responded that he really wasn't sure. I thought this would calm the situation down, but instead it had the opposite effect. Suddenly the chat veered towards him complimenting me, expressing regret that he didn't get to know me sooner and, recalling memories of the night we spent together.

He claims he doesn't talk to other girls this way — it's just he finds our connection exciting and somewhat frustrating, and I agree. After the chat got a little out of hand we agreed to cool things down. He says he still wants to be friends and chat regularly. To further complicate things, I'm moving to the city where he lives in the next few months. We've discussed hanging out then.

I know I want to continue chatting to him, but I worry that it's wrong on several levels: 1. He has a girlfriend, and I'm pretty sure she'd be upset by our correspondence. 2. I'm not in a relationship and I could easily develop feelings for him. 3. I'm not sure it's entirely possible to have a friendship with someone who you've expressed sexual desire towards, who's expressed the same towards you. All that said, I really enjoy talking to him and he says the same about me. If we make the effort to keep things more platonic what's the harm?

— Flirty Friend

Dear Flirty Friend,

Let those among us who have not experienced a strikingly similar situation raise their hands. Okay, everyone else, stone those guys, 'cause they're probably lying. (And also, with one arm raised, they can't defend themselves. Ha ha!)

Leviticus-style justice aside, Flirty Friend, these relationships happen. A lot. Like, so often that I wish I could print your question and give it to myself at ages eighteen, nineteen, and twenty-two, with a giant red headline: "YOU'RE NOT SPECIAL." Would've saved me a lot of staring out of windows while it rained!

Of course, Flirty Friend, I'm not saying you're not special. Of course you are. But this relationship is tired on many levels. There is no way to separate this "friendship" from lust. You got in touch with him out of a coy sense of "what if?" He wrote back, which made you feel butterfly-stomachy. You pumped up his ego with "I kinda like you." He pumped up yours with "I kinda like you back." Add in a dash of, "…but it's forbidden!" and you've got a sickly sweet cocktail that's taken out many a good man and woman. Don't be a statistic.

The important thing to remember here is that there's no tragic, star-crossed lovers element to this situation at all. You aren't being kept platonic by a cruel, unfeeling universe; you're being kept platonic because he wants to have his cake and eat it too. He gets to keep his girlfriend, then sigh into the phone about how great you are and how he can't explore a future with you because he's tied down by this stupid ball-and-chain girlfriend. Womp womp, amigo — it's tough to be adored.

Your question, "If it's platonic, then what's the harm?" is valid, but I'm pretty sure you can answer it yourself. This relationship won't ever be platonic unless you both make a conscious effort to steer it that way. As long as you are whispering your secrets to each other at three a.m., though, you're not "just friends." And reliving details of your hookup is an automatic disqualifier.

The most honest thing you can do is cut this thing off. Tell him you really enjoy talking to him, but can't in good conscience keep escalating the relationship. Then wish him well and gracefully disappear into the sunset. You deserve better than to be "the other woman."

You'll have your entire lives to get to know each other — platonically, flirtatiously, biblically, or all of the above. If your bond is really that strong, you can pick it up later — when you can both give your relationship the attention it deserves, without going behind anyone's back.